Massachusetts Winter Rental
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£228/Night
For 7 Nights £1,594
202.98 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Hot Tub
- Fireplace/Heating
£439/Night
For 7 Nights £3,073
1 Bedroom
1 Bathroom
Ocean View
Bed & Breakfast
- Spa
- Fireplace/Heating
- Ocean View
£322/Night
For 7 Nights £2,251
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
£257/Night
For 7 Nights £1,798
291.53 ft²
26 Guests
13 Bedrooms
13 Bathrooms
Bed & Breakfast
- Parking
- Air Conditioner
- Internet
£125/Night
For 7 Nights £872
1600 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£353/Night
For 7 Nights £2,474
12.55 ft²
15 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
£126/Night
For 7 Nights £882
1100 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
£228/Night
For 7 Nights £1,594
2002.09 ft²
9 Guests
4 Bedrooms
3 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
£192/Night
For 7 Nights £1,344
1350 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Ski Chalet
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£228/Night
For 7 Nights £1,594
172.22 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
£167/Night
For 7 Nights £1,168
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£116/Night
For 7 Nights £812
Why Choose Rent By Owner for your Massachusetts Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Massachusetts
How to Book Your Massachusetts Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Massachusetts
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Massachusetts, MA
Barnstable County
Cape Cod
Boston
Suffolk County
Middlesex County
North Shore
Essex County
Dukes County
Martha's Vineyard
Berkshire County
The Berkshires
Yarmouth
Frequently Asked Questions About Massachusetts Winter Rentals
1. What are the top Winter Rentals in Massachusetts?
There are a lot of options in Massachusetts. If you plan on staying in the Massachusetts area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Massachusetts:
- Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
- Leslie's Retreat: Spacious home ideally located to everything
- The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
- Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
- Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
- Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
- Two bedroom condo near to everything Ptown has to offer
- Lovely Dog Friendly Beach Home Close to Everything. 6 day stay open 6/28-7/4
- Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
- 4 Bedroom LUX House/with Pool Next Door
2. How many Winter Rentals are available in Massachusetts?
Currently, the total number of properties listed by RBO in 2026 is over 14113 in the Massachusetts area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Massachusetts.
More Rentals You May Like Near Massachusetts
1905.21 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Parking
- Air Conditioner
- Internet
£778/Night
For 7 Nights £5,447
1600 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£169/Night
For 7 Nights £1,180
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Skiing
- Fireplace/Heating
- Ocean View
£235/Night
For 7 Nights £1,643
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
£208/Night
For 7 Nights £1,459
850 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£237/Night
For 7 Nights £1,660
1500 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£167/Night
For 7 Nights £1,169
800 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£271/Night
For 7 Nights £1,901
1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£265/Night
For 7 Nights £1,855
600 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£187/Night
For 7 Nights £1,307
1250 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£248/Night
For 7 Nights £1,734
672 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£169/Night
For 7 Nights £1,182
1700 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£212/Night
For 7 Nights £1,485
